


Confessions of an Assistant.

by sleepyprincess



Category: Shall We Date?: Obey Me!
Genre: Aftercare, Biting, Brat training, Bratting, Cockwarming, Confessions, F/M, Fluff, Fluff and Smut, Hickeys, I really like the moon okay, Letters, Light Bondage, Lovebites, Manhandling, Masochism, Moonlight sex, Nipple Licking, Nipple Piercings, Nipple Play, Nipple Torture, Rough Sex, Sadism, Sex, Spanking, Teasing, Thighs, Training, Vaginal Sex, Window Sex, brat taming, thigh riding
Language: English
Status: Completed
Published: 2020-07-06
Updated: 2020-07-23
Packaged: 2021-03-04 19:42:48
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,304
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25111825
Author URL: https://archiveofourown.org/users/sleepyprincess/pseuds/sleepyprincess
Summary: Diva writes out her desires and lust for Lucifer.
Relationships: Lucifer & Main Character (Shall We Date?: Obey Me!), Lucifer (Shall We Date?: Obey Me!) & Reader, Lucifer (Shall We Date?: Obey Me!)/Original Female Character(s), Lucifer (Shall We Date?: Obey Me!)/Reader, Lucifer/Main Character (Shall We Date?: Obey Me!)
Comments: 5
Kudos: 69





	1. Chapter 1

**Author's Note:**

> I did it as a dare from a Discord server I'm in. 
> 
> YOLO.

Lucifer, I have a confession to make.

**I want you to break me, in body and mind**.

_I want you to scold me until my ears ring, a deserving punishment for something I’ve said/done. Yet through it all, not even your harsh words would hinder me; their only achievement would be to illicit an eyeroll deserving of such a lecture. With a twitch of anger flashing on your face, you would ask after witnessing such a brash act if I actually had the nerve to be so blatant in my disregard for your authority. This is when I would realize my first mistake, but it would be far from my last._

_The true question is with me being such an unrepentant brat—is it truly a mistake on my part if I get what I desire from you? Is it really a mistake, however, if I can’t help how I react to such aggressive displays of your temper? The tightness that coils in my lower belly at the way I crave for you to storm over to grab my chin with ferocity as you jerk my head up to face you. I can’t help the way my body reacts to the simple act of your touch against my skin. Nor can I help but contemplate what it would feel like to continuously defy you, near exhaustible attempts to get under your skin. As you glare down at me, I would reciprocate the hard look with an absence of fear. I would yank my head away from you and scoff, then tell you I don’t have time for this and stalk towards the door._

_I know for a fact that this would further intensify your fury. You would storm over to me—your power grants you extra speed—and put me in kabedon, shutting it with both your hands on either side of me. You would snarl in my ear about how I’m not going anywhere until you’re through with me, and how a brat like me won’t get away with speaking back to you like that. You love a challenge—the rigidity I would feel against my derriere would indicate so. I would turn around, entrapped by you as you hastily lock my arms behind me with one gloved hand._

_Of course, I would gasp from the abruptness of it all—however, this would do nothing to interfere with the urge to spit more of my bratty venom at you. I would goad you with my daring words into doing your worst (and best, as you have previously stated), before you tire of my mouth and peel one of your gloves off with your teeth. You would grab my chin once more, a few strands of your raven-colored hair now dangling from your face as your ruby eyes darken. With your free hand, you then would ball your glove up and shove it into my mouth._

_I would be startled, but not too surprised when you start undoing your tie with said free hand. Before I can even think to move, you ram your hips against mine to keep me still as you reach behind me for my wrists. Your erection would pulsate against my bare thigh—I would be wearing my trademark yoga shorts—as your lean down, your chin grazing at the top of my head as you bind my wrists together. Even though I would be gagged, I would still muffle out more bratty statements; I still find it in me to summon the reckoning within you._

_It would become increasingly difficult to focus with the relentless abuttal of your hardness against my hips. My muffled breath hitches against the damning gag that mutes my cries for more, always more. Noticing this would further prompt you to wedge your knee in the middle of my thighs, right under my soaked heat. My breath would hitch even more as I look up into your eyes, finally registering my second mistake: not wearing underwear that day. You would take heed of this with that devilish smirk of yours, gauging my reaction as you move your thigh upward and against my dilated clit. You know all too well how weak I am for thighs and my desire to ride yours, which would spur on your instinct to commence with my subjugation._

_With the elevation of your thigh, I would already be spasming from the sheer pressure alone. You would take your ungloved hand and creep it under the front of my tank top, your cool fingertips skimming underneath my breasts before you find one of the chains which dangle from my piercings. One of your graceful fingers would sweep at the piercing, which would trigger the most delicious sensations throughout my body. You would instantly decode this from the mewls that begin tumbling through your glove stuffed in my mouth. Even as you would force me to rut against your thigh with the door holding me upright, I would still cast you a glare of disobedience. Despite you being the Avatar of Pride, I still hold no trepidation as you flash me your signature sadistic smile._

_I would thrash against you, riveted and quivering as my hips move back and forth on your thigh. You live up to your title of the Malicious Sadist—you ensure this with a snatch of your thigh out from under my cunt. A nearly maddened growl would flutter from my smothered lips, in turn inducing that damned chuckle of yours. Seeing me begin to unravel at your hands and thighs would be a delight to you as you once more flick at my piercing. Your hand would snake around and give my ass a hard squeeze before lifting me against you, which would mark the start of my descent into the throes of indulgence. The glove you had crammed into my mouth would fall to the ground as a sexually pained cry erupts from my core. That alone demonstrates the effect you have on me; that not even mere gloves could confine the sexually driven melodies you have composed from my being._

_You know how I like it. Would you give in, to give me what I want? Would you not throw me over your shoulder and walk us over to our beloved window, all while tearing and twisting off a majority of my already minimal attire? I know you would. With the hold you’d have me in, you would deliver sharp, caustic slaps to my ass as I scream in response to each lashing. My masochistic tendencies—along with your desire to satiate your sadism—would stimulate you more, allowing you to relish in executing integrated pain and pleasure._

_“Is that it?” I would inquire with faux boredom, still hoisted over your shoulder while I recover from your delectable torment. Your clutch on me would secure much deeper than before, your nails submerging into the skin of my lower ass and upper thighs. You would set me off your shoulder, thrust me into the window and growl threats about how if I don’t stop speaking back to you, then you will make me stop. Ah, you would declare all this as you leave harsh, tenacious lovebites all over my neck and down to the crook in between my neck and shoulders. The hand that stuck me to the window would slither up my torso to toy with both of piercings ornamenting my breasts. Chills would pervade me fully, as would a throaty moan from the overstimulation beginning to cloud my willful mind. Much to my mirth, the work of a brat is never done. I would remember this when I glower up at you, declaring an unspoken challenge that I know you would not refuse. You do not frighten me in the least._

_As I have in the past, I have always sought out more punishment than reward from you. Before my imminent acquiescence, my gaze would remain unshaken as I speak back in the midst of your tangent about upping my “training”. All while, I would feel my arousal trickle down my thigh from the way you have manhandled me and touched me throughout this delightful ordeal. With an almost-shaking voice, I would remind you that it only took me a mere two days to recover from our first training session. I would push further by letting you know how it didn’t hurt as much as I had anticipated, and question whether or you truly live up to your reputation as the malicious sadist. Because true sadists hold no mercy, especially in the pursuits you and I engage in with one another._

_The darkening in your eyes before would return with a vengeance as you pull away from me, giving me an order turn facing the window. “Be still or suffer the consequences,” you command with a dangerously muted voice. Hearing you speak like this would come close to bringing about my orgasm—because that would signify just how much I’ve added fuel to the fire you carry within. You would walk off, leaving the front of my now exposed body revealing itself to the outside world. The cold of the window would electrify my piercings, which abut the glass as I start fidgeting against it._

_The first strike of the paddle to my behind would shock my system, sending my yearning for hedonism to new heights as I writhe against the chilled glass of the window. A surprised cry would fly off my lips, my own composure wavering as my pussy rubs against the glass. You would sense me trying to get off this way and deliver another blow to my ass, the music of the paddle echoing throughout your office. A rasped groan would purr from your throat as you order me to be silent. In the midst of your displeasure, you would not be able to help but palm at yourself at the sight before you; your bratty assistant, legs sprawled out across the window as she tries to not crumble to her knees. Because once I do, that is when I would fully surrender to you; despite it being short-lived._

_The both of us would be breathless at this point. Your hair would become disheveled; your cock would struggle against the confines of your trousers as your primal instincts begin to overpower ones of reason. My cheek would be pressed against the glass as I utter that one binding phrase—the one that would result in our ultimate undoing._

_“Do your worst.”_

_You would be done with these games. You would forego the paddle and, with a vexed growl, administer a series of ruthless spanks with full force by your bare hand; not even limiting yourself, despite my being human. I would be able to take it, my thighs shuddering from the burning arousal overtaking my own inhibitions. My cries of ecstasy would liberate themselves after each hit, your perfectly polished nails sinking into the skin of my ass after the final blow. I would come close to crumbling before you raise me upward, still against the glass. My thighs would be parted as you force your bottoms down, the heat of your erection prodding at my now dripping heat. A strained growl would flitter from your mouth before you hold me up by my thighs as you slam yourself into me. With the aid of your hips now carrying mine as you pump your girth into my pleading cunt, both of your hands would taunt and tease at my piercings. The sounds we bask in together would unite us in our hunt for euphoria, my body on full display for anyone who dares to look up at what is yours._

_And even as you empty your release into me, you would be far from done with me. I would continue twitching in your arms as I let out a shaky scoff, still challenging you to take me over and over. You would accept such a feat, knowing all too well of my testy element as you distend the walls of my cunt with your immense cock in various parts of your office. My ass would take the brunt of a good amount of your force, your hands alternating from toying with my piercings and marking my derriere until it has reached black and blue. You would leave the most intense of bites and hickeys all over my body, leaving no part of me unscathed as your release begins dribbling out of me; but that would not daunt you from pounding your cock into my swollen pussy, even as my sounds diminish from screaming so much that I would be left into a quavering, fluttering mess. Due to the multiple orgasms I know you would be determined to induce from me, my mind would begin to fog with nothing but how delirious having you in me feels._

_I would collapse in your arms, broken from what you have bestowed upon me. I would fade in and out of consciousness as you cradle me to you, carrying me over to the seat of your desk. You would sit down and maneuver me to where I would be straddling you, unfastening the tie from my wrists as my arms lazily snake around your neck. I would welcome being eased back on your cock as you describe how I am to warm it while you write a few more reports for Diavolo; you would go on to explain how should I move or make any disruptive noises, I am to expect to reap the consequences of my actions. One of your hands would give a piercing of mine a jerk before you get to work, all while I would be tasked with warming your cock. It would be strenuous to focus my attention on anything other than the way your cock palpitates in me. Through your stoic façade, you would quietly marvel at the way my inner walls accommodate your size beautifully._

_Regardless of how hazed my mind would be from the pleasure you’ve presented me with, the untamed brat would drive me to imprint the skin of your neck with my teeth. This would draw out a “tch” from you, preceding a firm slap to the side of my thigh as you purr at me not to push it. But from the way you would twitch inside of me, that would let me know you’re thriving from this unhurried agony as much as I. The heat would be pooling in my lower belly once more as the lips of my heat latch onto the hilt of you. My wetness would drip from me further upon me taking no heed to the warnings you give me as I alternate bites with licks. Indulging in such a bratty activity would reawaken me; knowing it would once more push you into executing more exhilarating punishments upon me. What would drive me into provoking you for what feels like the umpteenth time, especially, would be me feeling you tense up underneath me as you call my name with a labored warning tone. I would relish the rumbling underneath your words as your composure wavers from my impish tendencies. I would let out a tenacious moan in your ear, which would be what pushes you to throw your pen down and lift me upward with the growl I’ve come to cherish._

_You would position me to where I am only halfway on your cock now, your shaft wet from me as you envelop my waist with one arm. Your free hand would creep between us and tease one of my piercings with your adept fingers. My other piercing would be gifted with your mouth as you nibble and lick at it with your well-versed teeth and tongue. With my breasts being the most delicate parts of my body, such a gesticulation—especially done by you—would be my ultimate undoing. The frenzy in my body would stir, showing with multiple clenches of my cunt around you. My hands would clutch onto your stunning ebony locks as the arm around my waist glides downward to my ass, once more giving it a deep squeeze. It would then slide back upward, and to my midback to hold me in place as you continue your welcomed assault on my chest. The stifled moans and breaths from my lips would strive to crawl out of my throat, your name becoming a chant on my lips again. Hearing your bratty assistant in such a state of subjugation would spur you on as you shove me back onto your cock, to the hilt. You would seek to embellish my neck with extra dark purple flowers, drilling up into me as I am immobilized in your embrace. We would find ourselves in another pursuit of release, with your cum flowing up into me as you praise my ability to endure such an intensity. I would cum all over your cock and your lap, another shudder coursing through my body before I ultimately pass out on top of you._

_This is not the only scenario I imagine being in with you. Another one consists of you confiscating all of my underwear for an entire week, due to your need to alleviate the stress of all your hard work at RAD. You would keep it all in an undisclosed location for that time period, letting me know I won’t be needing them. This would be due to you wanting to fuck me anytime, anywhere; even if we’re not in the House of Lamentation. I could be writing some pieces and you would easily lift me up and lower me onto your cock. I could be trying to make myself something to eat in the kitchen, and you would bend me over the counter and take me there. I could even be sleeping, and you have full permission to touch me and integrate yourself with me however you’d like. Even as I wake up, I want you to hold me against you as you snap your hips up into me and dare me to challenge you. I would ready a snarky—albeit sleepy—response and say it, but that would only propel you to drive yourself further into me. This would subdue me into sleep-filled moans and whines; you would emit quiet purrs and growls in my ear about how I am to satiate you, and how it is my fault for enticing you into such a state of carnal mind. Naturally, I would take full responsibility._

_I want you in every fathomable scenario—riding your thigh as you work at your desk, waiting for you in your office in nothing but fishnets and your coat, misbehaving in public so you can further inflict more punishment on me once we are in private—or, depending on your mood, you could reach me my lesson in a dark corner of wherever we would go. I could go on about each one, but I know you have more than enough work to do; I dare not waste anymore of your time with my fancies. What I dare to confess is how I crave for you to break me into subjugation, to take me until I lose all sense of my mind and body until I am fit into your perfect image. Break me until I lose all sense of time, space and reality. Leave me broken, ecstatic and unable to sit for a month. Do whatever you deem me worthy of; whatever my body can handle, you are free to use all my holes as you please. Train me over and over until you get tired of me, and even then—I would continue to challenge you. I confess, I rambled for longer than I had anticipated…apologies._

_Thank you for reading up to this point, and I do hope I have not angered you in ways we both would be unable to enjoy. I do hope you enjoy the rest of your evening. Be well, Morningstar._

_Your rambunctious assistant,_

**Diva~**


	2. Borrow the Moonlight.

**Summary for the Chapter:**

> Diva writes out her softer confessions.
> 
> Sensual fluff.
> 
> Confessions, Part II.

**Notes for the Chapter:**

> I was dared to write out this second part. It's shorter, due to it being my first attempt at some kind of fluff.
> 
> YOLO.

_Once you deem my punishments adequate for my transgressions, you would gift me with a reward in the form of a hot bath. You would carry me to the bathroom, my body slack with a welcomed exhaustion from our preceding activities. Upon us both being submerged in the hot water, I imagine you would be murmuring praises about how well I did in enduring my punishments. You would massage my sorest areas with a tentativeness so secret to most, still sneaking in fondles and gropes for a gentle rise in me. You do so, knowing it’s exactly what I wanted; along with the kisses and laps you lay upon my beautifully marked skin, the ones you’ve gifted me with._

_Another scenario of the softer side: I would be wandering in the gardens of HoL at night, unable to sleep. You would suddenly appear out there, wondering what I was doing up so late. We would speak about how I can’t sleep, and you would offer your arm to me as we take a stroll. We chat idly, the looming tension between us menacing as we come upon a clearing. Flowers encompass the area as you guide me into it, laying out your coat for us to sit on as you tug me down to sit next to you. My head is leaning against your shoulder as we move closer to one another, our legs now abutting one another before. We gaze up at the moon, which is full and splendent as you run a hand up and down my back. While we converse, I feel said hand start to slip underneath the shirt I’m wearing. Your fingers would trail along my bare skin in light, feathered movements just to touch me. You wouldn’t seek to stimulate at first; it would be from being unable to fathom not touching me, the trails turning into unplanned patterns. Goosebumps would make an appearance along my arms, but I would not bring that to your attention._

_Throughout our exchange—which is laced with banter and flattery—your clever hand would skip up from my shirt to cup at my cheek. You would turn my face to meet yours, speech deeming itself unneeded as your thumb caresses at my skin. I would find myself lost—once more—in those ruby red eyes, before you would steadily lean in for a chaste kiss. I would almost be convinced I imagined it, due to how delicate the union of our lips would be. Yet, I would still be able to feel your warmth from it; that alone would let me know the sincerity behind it._

_I would be rendered speechless by what would follow. Your forehead would nestle against mine, both our eyes lidded and barely open from how intoxicated we would be by each other’s presence. However—you would gift me with a varying kind of kiss, involving words. You would whisper sweet musings you’ve long locked away in your heart, your pride refusing to permit you liberation in expressing them. Such avowals would leave me breathless, a quiet gasp escaping my lips. As cunning as you are, you would steal this opportunity to blindside me with another kiss; this one having more of a wonderful force than before._

_Through the contact of our lips, I would feel the affection seeping from you as your hand continues holding my cheek. I would gain my own courage and move one of my hands to hold yours upon my face; the other would settle itself on your other hand on the grass. Our fingers would interlace as soon as you lay us down onto the grass, each keep deepening with an urgency differing from that of our normal encounters with one another. Unhurried, you would move to be in the middle of my legs; we would move our hips against one another as our hands hungrily clutch onto as much of each other as possible. I would feel your rigidity against my heat, unmatched by our newfound patience as we would take our time in liberating one another of our attire. The flowers surrounding us would dance around us, the magic in the air whisking us away to a world of our own as we adorn each other with tender bites and kisses along one another’s skin. The luminescence of the moon would intensify upon you entering me, our foreheads pressed together again as we lock into a fierce embrace._

_We would borrow the moonlight as you thrust in and out of me, taking your time as we murmur praises and shower each other in fevered touches. Arousal and affection would integrate into one, our unrushed desire for release permitting us time to relish in exploring the most intimate parts of each other. The sounds shared between you and I would be the most uninhibited, our breaths hitching as your cock would graze at my most intimate spot. Hickeys would still be left along your skin, as they would be left along mine as we give each other unrepressed eye contact. I would clench around you slowly, with a tireless strength that would send us both reeling into cloud nine. As we reach our climax in harmony, you would grab me by the back of my neck and pull me into a wild kiss. The music of our pleasure would invade our mouths, welcomed as we feel each other’s need for one another through our gesticulations._

_I apologize once more for the abundancy of words. I am not one to express my softer feelings, as I am still adjusting to them. I thank you for reading this in its entirety, and I hope you enjoyed it as much as I enjoyed writing it._

_Your impetuous assistant,_

_Diva~_


End file.
